GBM

5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide

Created:	2015-04-03
Last modified:	2021-03-13

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Chemical Details
Formal Charge	0
Atom Count	61
Chiral Atom Count	0
Bond Count	63
Aromatic Bond Count	12

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Chemical Component Summary
Name	5-chloro-N-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide
Synonyms	Glibenclamide; Glyburide
Systematic Name (OpenEye OEToolkits)	5-chloranyl-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxy-benzamide
Formula	C₂₃ H₂₈ Cl N₃ O₅ S
Molecular Weight	494.004
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(NC1CCCCC1)NS(=O)(=O)c3ccc(CCNC(=O)c2c(OC)ccc(Cl)c2)cc3
SMILES	CACTVS	3.385	COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3
SMILES	OpenEye OEToolkits	1.9.2	COc1ccc(cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3)Cl
Canonical SMILES	CACTVS	3.385	COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3
Canonical SMILES	OpenEye OEToolkits	1.9.2	COc1ccc(cc1C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)NC3CCCCC3)Cl
InChI	InChI	1.03	InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
InChIKey	InChI	1.03	ZNNLBTZKUZBEKO-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB01016
Name	Glyburide
Groups	approved
Description	Glyburide is a second generation sulfonylurea used to treat patients with diabetes mellitus type II.[L8123] It is typically given to patients who cannot be managed with the standard first line therapy, [metformin].[L8123] Glyburide stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations.[A183617] Glyburide was granted FDA approval on 1 May 1984.[L8117] A formulation with metformin was granted FDA approval on on 31 July 2000.[L8120]
Synonyms	Glyburide Glibenclamidum 5-chloro-N-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide Glibenclamide 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea 1-((p-(2-(5-chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea Glibenclamida
Brand Names	Micronase Pro-glyburide Glyburide Micronized and Metformin Hydrochloride Teva-glyburide Glyburide GlyBURIDE Apo Glyburide Tab 5mg Glyburide-Metformin Hydrochloride Sandoz Glyburide Micronized Glyburide Diabeta 5mg Apo Glyburide Tab 2.5mg Amglidia Glyburide Tablets 5mg Penta-glyburide - 5mg Med Glybe Tab 5mg Euglucon Diabeta Tab 2.5mg Nu-glyburide Tab 5mg Ava-glyburide Glucovance Ratio-glyburide Penta-glyburide - 2.5mg Riva-glyburide Dom-glyburide glyBURIDE Diabeta Tab 5mg Diabeta Tablets 2.5mg Glyburide-metformin Hydrochloride Glynase Mylan-glybe Glyburide-5 Tab 5mg Glyburide and Metformin Hydrochloride Nu-glyburide Tab 2.5mg Glyburide Tablets 2.5mg PMS-glyburide Ntp-glyburide Glyburide (micronized) and Metformin Hydrochloride Med Glybe Tab 2.5mg Glyburide and Metformin DiaBeta
Indication	Glyburide is indicated alone or as part of combination product with metformin, as an adjunct to diet and exercise, to improve glycemic control in adults with type 2 diabetes mellitus.[L8120,L8123]
Categories	Alimentary Tract and Metabolism Amides BCRP/ABCG2 Substrates Blood Glucose Lowering Agents BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Drugs Used in Diabetes Hypoglycemia-Associated Agents Insulin Secretagogues OAT1/SLC22A6 inhibitors OATP2B1/SLCO2B1 substrates Oral Hypoglycemics P-glycoprotein inhibitors Photosensitizing Agents Sulfones Sulfonylureas Sulfur Compounds
ATC-Code	A10BB01
CAS number	10238-21-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
ATP-binding cassette sub-family C member 8	MPLAFCGSENHSAAYRVDQGVLNNGCFVDALNVVPHVFLLFITFPILFIG...	unknown	modulator
Sulfonylurea receptor 1, Kir6.2	MPLAFCGSENHSAAYRVDQGVLNNGCFVDALNVVPHVFLLFITFPILFIG...	unknown	blocker
ATP-binding cassette sub-family C member 9	MSLSFCGNNISSYNINDGVLQNSCFVDALNLVPHVFLLFITFPILFIGWG...	unknown	modulator
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
Phospholipid-transporting ATPase ABCA1	MACWPQLRLLLWKNLTFRRRQTCQLLLEVAWPLFIFLILISVRLSYPPYE...	unknown	inhibitor
Mitochondrial ATP-sensitive potassium channel	MLSRKGIIPEEYVLTRLAEDPAKPRYRARQRRARFVSKKGNCNVAHKNIR...	unknown	inhibitor
Carnitine O-palmitoyltransferase 1, liver isoform	MAEAHQAVAFQFTVTPDGIDLRLSHEALRQIYLSGLHSWKKKFIRFKNGI...	unknown	inhibitor
Cystic fibrosis transmembrane conductance regulator	MQRSPLEKASVVSKLFFSWTRPILRKGYRQRLELSDIYQIPSVDSADNLS...	unknown	antagonist
Transient receptor potential cation channel subfamily M member 4	MVVPEKEQSWIPKIFKKKTCTTFIVDSTDPGGTLCQCGRPRTAHPAVAME...	unknown	inhibitor
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
ATP-binding cassette sub-family C member 3	MDALCGSGELGSKFWDSNLSVHTENPDLTPCFQNSLLAWVPCIYLWVALP...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate,inhibitor
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	inhibitor
Solute carrier family 15 member 1	MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...	unknown	inhibitor
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
Solute carrier family 15 member 2	MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...	unknown	inhibitor
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	inhibitor
ATP-binding cassette sub-family C member 2	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	inhibitor
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
Solute carrier family 22 member 7	MGFEELLEQVGGFGPFQLRNVALLALPRVLLPLHFLLPIFLAAVPAHRCA...	unknown	inhibitor
Solute carrier organic anion transporter family member 2B1	MGPRIGPAGEVPQVPDKETKATMGTENTPGGKASPDPQDVRPSVFHNIKL...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682